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Challenging Hikes Toronto

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๐Ÿฅพ Silent Lake Hike

๐Ÿฅพ Silent Lake Hike

Sat, Sep 19, 1:00 PM
From Try Toronto: Newcomers, Friends & Local Experiences

Escape the city and discover Silent Lake Provincial Park - peaceful forest trails, granite ridges, crystal-clear water, and beautiful viewpoints over one of Ontarioโ€™s few motor-free lakes. Weโ€™ll hike a 15 km loop at a relaxed pace with breaks for photos and enjoying the scenery. The trail is easy to moderate, but you should feel comfortable walking for 5-7 hours on uneven terrain with some hills and rocky sections. After the hike, weโ€™ll relax at the beach for a snack or head to a nearby restaurant together. **โ˜€๏ธ What to expect:** โ€ข Guided 5-7 hours loop hike through Silent Lake Provincial Park โ€ข Beautiful forest trails and rocky Canadian Shield landscapes โ€ข Scenic lookouts over the lake โ€ข Plenty of photo opportunities โ€ข Friendly group and a relaxed pace โœจ **Price:** $65 - participants without their own transportation ๐Ÿšถโ€โ™€๏ธ $40 - participants driving their own car ๐Ÿš— (without passengers) - promocode **SELFDRIVE** $25 - participants driving their own car ๐Ÿš— and willing to take 3+ passengers (driver pays for gas themselves) - promocode **DRIVEROFF** **Price includes:** guidance throughout the hike, light snacks and transportation coordination for participants without cars. ๐Ÿ“ **Meeting place:** Vaughan subway station โ€ผ **Difficulty**: Easy to Moderate **๐Ÿ™‹โ€โ™€๏ธ Guide:** Kate - an ambassador for hiking and outdoor adventures in all seasons. She completed 124 km of the Camino in just 6 days. A coach and advocate for the idea that therapy can save everyone. And what could be more therapeutic than walks in nature?! **Register here or on [TryToronto website](https://trytoronto.org/events/silent-lake)**

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1 attendee

Hike with Lorne O

Sun, Oct 25, 3:00 PM
From Mosaic Outdoor Club of Ontario (GTA+)
4.7
5 attendees
Epic #5 - The Lavielle Loop

Epic #5 - The Lavielle Loop

Wed, Sep 2, 9:00 AM
From Wilderness Union Toronto - Outdoor Adventure and Hiking Club
4.7

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/epic-5)** ***Welcome to The Epics!*** ***Through this series, we will embark together on five of the most legendary and challenging adventures anywhere in Ontario.*** **History** Deep in the interior of Algonquin Park lies a chain of lakes that remains a bucket list trip for serious paddlers. The Lavieille Loop is a high-endurance expedition named after one of the most beautiful lakes in a park full of incredible scenery. This is a route of extremes: from the crystal-clear expanse of **Lake Lavieille** to the winding, moose-heavy waters of the **Crow River**, culminating in the legendary 5.5km **Dickson-Bonfield portage**, this is a true test of grit. This expedition is inspired by the Meanest Link, a legendary challenge created by our friends and partners at Algonquin Outfitters. Designed by Alex Hurley and Gord Baker as a tribute to AOโ€™s founder, Bill Swift Sr., the Link was built to push the limits of exploration and self-reliance. While our loop covers a specific, scenic section of this historic network, weโ€™ve designed this Epic to channel that same spirit of adventure and respect for the parkโ€™s heritage. Learn more about the history and the original route of the Meanest Link on the [Algonquin Outfitters website](https://algonquinoutfitters.com/about/meanest-link-history/). โ€ **What You Need to Know** This journey is a true ode to Algonquin Park. Weโ€™ve carved out a nearly 100km route, taking us from the massive waters of Lake Opeongo, along the winding Crow River, and into the remote reaches of Lake Lavieille before heading back down to Opeongo. By doing this in early September, we catch the park at its absolute best: the bugs are gone, the weather is beautiful, and the wildlife is active along the riverbanks. Awaiting us in the second half of our journey is the notorious Dickson-Bonfield portage. At over 5km,this is the longest single portage in Algonquin Park. Itโ€™s relatively flat but a huge challenge and, once you set your canoe down at Bonfield Lake, youโ€™ll have earned your place among the most dedicated paddlers in the province. This trip requires a high level of fitness and a genuine willingness to embrace the challenge of a 5km trek with a canoe on your shoulders. For those willing to take on the challenge, this offers the most rewarding sense of accomplishment you can find on the water. **What's Included:** * *2 expert guides with advanced wilderness skills and medical training* * *Rentals for lightweight canoes, PFDs and paddles* * *All camp meals, cooking equipment and mess kits* * *All safety equipment (including first aid kits and water purification)* * *Tents and all the camping equipment you'll need (sleeping bags and pads are available for rent)* * *All permits and campsite bookings for the whole trip* * *A preparatory information session* * *Detailed trip plan with packing lists, maps and the indigenous history of the route we're following* * *Extensive planning to ensure your safety throughout the adventure* * *A custom, iron-on patch to immortalize your unforgettable adventure* ***Epics are mentally and physically demanding adventures, and participation isnโ€™t automatically guaranteed. These expeditions require skill, determination and teamwork to get through.*** ***To help ensure a safe and rewarding experience for all, anyone who has not previously completed an Epic will need to fill out a short questionnaire so we can assess readiness together.*** ***Your level of fitness and outdoors experience will play a role in this process. Having certain adventures under your belt will ensure you have the right skills and preparation for these kinds of experiences. These include:*** * ***Any Wilder Series adventure, including the upcoming Wilder Loop*** * ***Any Survivalist Series adventure, including Introduction to Navigation or Cold Exposure*** * ***Canoe Foundations Clinic*** * ***Hilton Falls Mega*** * ***Any other adventure with 4 or 5 star difficulty*** ***If you register for an Epic and are not approved, you will receive a refund in full.*** **Highlights** **An Epic Challenge -** Our longest and most ambitious epic will be the ultimate reward. **Dickson-Bonfield Portage -** The legendary portage spans 5.4km and is the longest single carry in the park. โ€**Secret Lake Sanctuaries** \- True crown jewels of the Algonquin interior\, there are no easy routes to the lakes we will be seeing\, which keep them incredibly quiet and pristine\. **Event cost: $1185+HST. $50 optional transport also available. Please register [here.](https://www.wildernessunion.com/adventures/epic-5)** **About Wilderness Union** Wilderness Union is deliberate about building an outdoors community that connects you to the life-changing magic of the outdoors and helps you find your people. Members range from 20-40 years old. The group is a mix of GTA locals and newcomers to Toronto from within Canada and abroad. Attendance numbers on Meetup don't reflect our actual event attendance - we typically have 15-20 community members at each event. Large enough that there's someone new to meet but small enough that it's not overwhelming! ***Learn more at our website [www.wildernessunion.com](https://www.wildernessunion.com/)***

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3 attendees
HikeFit: Earl Bales โ€“ Steep Hills Fitness Hike โ€“ L3 (Moderate)

HikeFit: Earl Bales โ€“ Steep Hills Fitness Hike โ€“ L3 (Moderate)

Wed, Sep 2, 10:30 PM
From Ready, Set, Trail
5.0

Ready to sweat it out on the hills? Join us for a HIIT-style hill training hike This hike is part of the **HikeFit Series**, a collection of fitness-focused hikes designed to build strength, endurance, and overall hiking fitness. Weโ€™ll challenge you with steep climbs, rugged terrain, and a high-intensity workout. This isnโ€™t a fast-paced hike, but it is **intense**. Weโ€™ll tackle multiple **very steep hills** in intervals, with plenty of chances to catch your breath, recover, or skip hills if needed. This hike is designed for intermediate hikers, but itโ€™s **beginner-friendly** since you can skip as many hills as you need. Itโ€™s perfect for anyone looking to **get stronger, improve endurance, and boost their hiking fitness** at their own pace. **Weather-Dependent Notice:** The hike is a go, **(light)** rain or shine; However, if there's a risk of excessive mud making the hills too slippery, the hike will be canceled with around 24 hoursโ€™ notice. **Distance & Duration:** * **Length of hike:** \~4 km * **Event duration:** \~1.5 hours * **Trail maps:** Random hill at Earl Bales park * **Difficulty level:** L3 (Level 3/Moderate) * Terrain: L4 * Pace: L2 * Distance: L1 **What to Bring:** * **Water:** 1\~2 liters * **Extras:** Hiking pole (Highly recommended) * **Required Gear:** Hiking boots or Trail Runners with good grip, Headlamp, and [Microspikes](https://kahtoola.com/traction/microspikes-footwear-traction/?srsltid=AfmBOoqq-URDFRgNAISoLYH1l1cSLKeXOTSuU6EqUC6VupfLNZAGRg8P) **Costs:** * **Member Event fee:** FREE EVENT **Travel Coordination:** * No Travel Coordination for this Event, Meeting at Starting Point **Event Guidelines:** * **Punctuality,** Please arrive on time so we can start promptly. We won't be able to wait for more than 5min past the start time * **Pack out everything you bring** (including nut shells, fruit peels, etc.) to help keep our trails clean. * **RSVP:** Only those marked as โ€œGoingโ€ and have confirmed travel details (if requested) are eligible to attend the event. * If your **plans change** and you are no longer able to attend, please update your RSVP as soon as possible. * **No-shows** without prior communication may result in removal from future events. * **Weather Considerations** The hike is a go (light) **rain or shine**, so please be prepared for the conditions. for example, If itโ€™s expected to rain, waterproof gear (like a jacket or shoes) * **Pets:** please check with the organizer for details before bringing your pet. Looking forward to seeing you on the trail

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2 attendees
Hello Fall Colours: Dorset Hike & Lookout Tower

Hello Fall Colours: Dorset Hike & Lookout Tower

Sun, Sep 20, 11:00 AM
From Wilderness Union Toronto - Outdoor Adventure and Hiking Club
4.7

**Please note the only way to register for this adventure is on [our website.](https://www.wildernessunion.com/adventures/dorset-hike-and-lookout)** **Not every good trail makes it into a guidebook, and this hidden gem sure hasn't.** Tucked just southwest of Algonquin, it's a route we keep close for our members: rolling rock outcrops, quiet beaver ponds, and wide ridges that open into sweeping views when you least expect them. In September, the whole forest turns to a radiant display of red, orange, and gold; the kind of colours that makes you stop mid-stride. Welcome to fall in Ontario. We'll cover 7.5 km at a comfortable pace, with plenty of time to take it in before stopping for lunch at one of the best views on the route. It's a moderate hike, and a solid choice if this is your first time out on trail. From the trailhead, it's a short drive to Dorset. The tower was first built in 1922 as a fire lookout and rebuilt in 1967 into the structure that stands today. Climbing to the top puts you level with the treetops and gives you a panorama of the hills and lakes around Lake of Bays, all dressed in their fall colours. It's one of Ontario's most recognizable lookouts, offering a totally different perspective after a morning spent within the tree canopy. **Please note that anyone not taking the WU transportation will need to purchase their own tower access pass.** โ€ **Accessibility** Wilderness Union is committed to making our adventures as accessible as possible. If you wish to make an accommodation request relating to a disability or provide feedback, please do so by sending an email to [info@wildernessunion.com](mailto:info@wildernessunion.com) **Highlights** **The Lookout Tower Climb:** The observation deck sits 142 metres above Lake of Bays, with a 360 degree view over the surrounding hills and lakes. **A Trail Off the Map:** A quiet, little-known route kept for Wilderness Union members, far from the lineups that build up around Dorset in the fall. **Fall Colours:** Red, orange, and gold scattered across the Canadian Shield. **Event cost: $75+HST (for explorer members) + $60 optional transport available.** **Register [here.](https://www.wildernessunion.com/adventures/dorset-hike-and-lookout)** **About Wilderness Union** Wilderness Union is deliberate about building an outdoors community that connects you to the life-changing magic of the outdoors and helps you find your people. Members range from 20-40 years old. The group is a mix of GTA locals and newcomers to Toronto from within Canada and abroad. Attendance numbers on Meetup don't reflect our actual event attendance - we typically have 15-20 community members at each event. Large enough that there's someone new to meet but small enough that it's not overwhelming! ***Learn more at our website [www.wildernessunion.com](https://www.wildernessunion.com/)***

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2 attendees
๐ŸŒ…๐Ÿ‚ Sunset Walk: Glen Stewart Ravine & The Beach Boardwalk

๐ŸŒ…๐Ÿ‚ Sunset Walk: Glen Stewart Ravine & The Beach Boardwalk

Wed, Sep 2, 10:30 PM
From No Such Thing As Bad Weather Walking & Hiking Group!
4.8

# ๐ŸŒ…๐Ÿ‚ Sunset Walk: Glen Stewart Ravine & The Beach Boardwalk ### A Short Fall Walk, Ice Cream & Sunset by the Lake Looking for an easy way to spend a fall evening? Join us for a relaxed **sunset walk through Glen Stewart Ravine**, followed by ice cream and a stroll along the Beach Boardwalk as the sun goes down. Weโ€™ll start at **Main Station** and make our way through the neighbourhood toward Glen Stewart Ravine. After enjoying the ravine and the fall colours, weโ€™ll stop at **Edโ€™s Real Scoop** for ice cream. ๐Ÿฆ Then we'll head toward the lake and walk along the **Beach Boardwalk**, taking in the evening light, the water, and the changing colours of the season. We'll finish at **Woodbine Beach**, where we'll take a little time to enjoy the sunset before wrapping up. This is a **short, easy walk of about 90 minutes**. Thereโ€™s no rushing and no trying to conquer a trail โ€” just a beautiful evening, something sweet to eat, and good people to enjoy it with. ๐Ÿ“ฑ Don't forget to join our **WhatsApp Group โ€“ [CLICK HERE](https://chat.whatsapp.com/H59mSCbsAi018gYANrKAnc)** *** ## ๐Ÿšถโ€โ™‚๏ธ What We'll Do We'll meet outside **Main Station** and make our way toward Glen Stewart Ravine. Along the way we'll: * ๐Ÿ‚ Walk through Glen Stewart Ravine * ๐ŸŒณ Enjoy the fall colours * ๐Ÿฆ Stop at **Edโ€™s Real Scoop** for ice cream * ๐ŸŒŠ Head down toward the lake * ๐Ÿšถโ€โ™‚๏ธ Walk along the Beach Boardwalk * ๐ŸŒ… Enjoy the sunset at Woodbine Beach The entire walk is approximately **90 minutes**, depending on the pace of the group. This is a **social walk**, so we'll take our time and enjoy the evening. *** ## ๐ŸŒ… Sunset & Weather This walk is all about enjoying the transition from **afternoon into evening**. The temperature can feel cooler near the lake, especially after sunset, so bring an extra layer. We'll walk **rain or shine unless severe weather makes the walk unsafe**. *** ## ๐Ÿงข Meetup Details ๐Ÿ“ **Meetup Location:** Outside **Main Subway Station** ๐ŸซŽ Look for me in my **Moose Hat!** โฐ **Meetup Time:** **6:30 PM sharp** I will only wait **5 minutes**. **Early is on time. On time is late.** ๐Ÿ **End Point:** **Woodbine Beach** *** ## ๐ŸŽŸ๏ธ Meetup Fee **$5 cash in person or e-transfer** ๐Ÿ“ง **mathewmaclean@hotmail.com** This fee helps support the group and allows us to continue organizing events throughout Toronto. **Ice cream is not included in the Meetup fee.** ๐Ÿฆ *** ## ๐ŸŽ’ What to Bring ๐Ÿ’ง Water ๐Ÿ‘Ÿ Comfortable walking shoes ๐Ÿงฅ A light jacket or sweater ๐Ÿฆ A few dollars for ice cream ๐Ÿ“ฑ Your phone or camera for sunset photos *** ## ๐ŸŒˆ Who Is This For? This walk is great for: * Anyone looking for an easy evening outing * People who enjoy walking but don't want a long hike * Anyone who loves fall colours * Ice cream lovers ๐Ÿฆ * People who want to meet others in a relaxed setting * Anyone who wants to watch the sunset by the lake The activity is the container. **The people you meet along the way are the real experience.** *** **REMEMBER:** You're welcome to RSVP ahead of time or just show up on the day if you're unsure about your schedule. Sometimes things happen and events may need to be cancelled or changed, so please keep an eye on the event page for updates. ๐Ÿ‘ค **Organizer: Mathew** Questions? Post on the event wall or email: ๐Ÿ“ง **torontomoviesandoutings@hotmail.com** **Come for the walk.** **Stay for the ice cream.** **Watch the sunset with us.** ๐ŸŒ…๐Ÿฆ

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20 attendees
430kMonthly events
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Frequently asked questions

Meetup connects people through shared interests. Whether you're into hiking, tech, or a particular hobby, it helps you find events and groups to join.

Use Meetup to search for hiking events in Toronto. You can filter by the activity type to find challenging hikes that match your experience level and interest.

Yes, there are several hiking groups in Toronto. These groups organize regular events and hikes, including challenging ones, allowing you to meet other outdoor enthusiasts.

Absolutely! Meetup lets you join as many groups as you like. It's a great way to increase your chances of finding hikes that meet your interests and schedule.

Some hikes may require special gear based on their difficulty. Always check the event details on Meetup, which often include gear recommendations from the organizers.

Many Meetup events are free, but some may have a fee. It varies by event and organizer, so check the event's description for specific details.

Once you find a hike you'd like to join, click on the event and use the RSVP button to indicate your attendance. It's simple and updates the organizer immediately.

Meetup covers a variety of activities, from relaxed to challenging. Join groups and choose events that fit your interest; challenging hikes are just one option.

Yes, if you're interested in leading a hike, you can organize an event on Meetup. You'll need to start your own group or join one as an organizer.

While Meetup brings together people with common interests, the level of expertise varies. Engaging actively helps meet people aligned with your hiking skill level.

Meetup encourages group interaction which can be safer, especially for challenging hikes. Always follow event guidelines and connect with others at the event.

Meetup facilitates connections but can't control weather or trail conditions. Always check local reports and prepare accordingly.

Availability of hiking events may vary by season. Toronto has active outdoor communities, but check regularly to see upcoming hikes.

Most hikes are in-person, and group meetings are scheduled to explore trails together. Always check event details, as some activities might also be virtual talks or preparations.

Absolutely. While this page focuses on challenging hikes, Meetup caters to all skill levels. Look for beginner-friendly groups and grow your skills with others.